1-Indanone → 2,3-Dihydro-N-benzyl-1H-inden-1-amine

HRID 265228

Reaction equation

HRID 265228 reaction equation
[C:1]1(=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.BrCC(OCC)=O>[Pd]>[CH:1]1([NH:18][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 67351-IndanoneHCID 7504BenzylamineHCID 7748Ethyl bromoacetate

Product 1

HCID 101307242,3-Dihydro-N-benzyl-1H-inden-1-amine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The amino acid was synthesized as described by Miyake, et al., Takeda Kenkyushoho 44: 171-185 (1985). [Chem. Abstr. 106: 156830 (1987)]. N-(1-indanyl)-benzylamine was prepared by reductive amination of 1-indanone with benzylamine, and alkylation of the amine by ethyl bromoacetate. The benzyl group was cleaved by hydrogenolysis over palladium. Saponification of the ethyl ester gave the amino acid, which was converted to the Boc derivative by the standard procedure described in Example III.

Workup

  1. customThe amino acid was synthesized

Sources & evidence

ORD record
ord-7f2f1b591a2445f18913943b894b5a90
Source dataset
uspto-grants-1997_07
Patent number
US05648336

Linked notes

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